P-nitrobenzene sulphonyl guanidine and process for making it



Patented Jan. 28, 1941 UNITED STATES PATENT OFFICE P-NITROBENZENE SULPHONYL GUANIDINE AND PROCESS Philip Stanley Winnek,

FOR, MAKING IT Riverside, Conn., assignor to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Original 1940, Serial No. 320,430.

application February 23,

Divided and this application September 19, 1940, Serial No. 357,499

2 Claims.

mula:

NOOSOa-NH-(fi-NH:

The compound of this invention is useful as an intermediate in the preparation of chemotherapeutic agents.

This is a divisional application of my copending application Serial No. 320,430 filed February 23, 1940, which matured into U. S. Patent 2,218,490 on October 15, 1940.

While the present invention is not limited to any particular method of preparing this compound, I have found that good yields of the o p-nitrobenzene sulphonyl guanldine can be obtained by adding p-nitrobenzene sulphonyl chloride to an aqueous solution of guanidine and keeping the pH of the mixture slightly on the alkaline side by the addition of sodium hydrox 25 ide. After the reaction is complete, the p-nitrobenzene sulphonyl guanldine is separated by filtration and purified by crystallization from water.

p-Aminobenzene sulphonyl guanidine can be prepared by reducing the nitro compound.

The invention will be described in greater detail in connection with the following specific example. The parts are by weight except in the case of liquids which are expressed in corresponding parts by volume.

Exmru:

p-Nitrobenzene sulphonyl guanidine Ten parts of guanidine hydrochloride (0.1 mol) was dissolved in 75 parts 01' water and the pH adjusted to 8-9. The solution was warmed to 50-60 C. and kept at this temperature while a slurry of 25 parts (0.113 mol) of p-nit'robenzene sulphonyl chloride was added slowly with mechanical stirring. The pH was kept at 8-9 by the addition of 40% sodium hydroxide solution. At theend of the reaction the solution was cooled and filtered from the separated solid. The pnitrobenzene sulphonyl guanidine was recrystallized from hot water.

What I claim is:

1. The compound having the following for- 2. The process of producing the compound of the formula:

which comprises reacting guanidine with p-nltrobenzene sulphonyl chloride and separating the resulting product.

PHILIP STANLEY WINNEK. 

